Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C16H19NO4 |
| Molecular Weight | 289.3264 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)OC(=O)C3=CC=CC=C3)C(O)=O
InChI
InChIKey=GVGYEFKIHJTNQZ-RFQIPJPRSA-N
InChI=1S/C16H19NO4/c1-17-11-7-8-12(17)14(15(18)19)13(9-11)21-16(20)10-5-3-2-4-6-10/h2-6,11-14H,7-9H2,1H3,(H,18,19)/t11-,12+,13-,14+/m0/s1
Benzoylecgonine can be found in medical products as a topical muscle relaxer, anesthetic or to relieve muscle pain. It is also a metabolite that is created in the liver after drug use, in particular, the use of cocaine, making it the main compound tested for cocaine use during drug screenings. The legality of this compound is in the grey area. Cocaine is a schedule II drug, but the metabolite is not the drug, it’s a by-product of its use. So detection of actual use is impossible, as its already a metabolite. But the use of cocaine and cocaine based drugs like crack is detected, through this compound. Benzoylecgonine is formed in the liver by the metabolism of cocaine, catalysed by carboxylesterases, and subsequently excreted in the urine. It can be found in the urine for considerably longer than the cocaine itself which is generally cleared out within 5 days
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| In vitro stability of cocaine in whole blood and plasma including ecgonine as a target analyte. | 2001 Apr |
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| Rapid confirmation/quantitation of ecgonine methyl ester, benzoylecgonine, and cocaine in urine using on-line extraction coupled with fast HPLC and tandem mass spectrometry. | 2001 Jan-Feb |
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| Importance of vacutainer selection in forensic toxicological analysis of drugs of abuse. | 2001 Jul-Aug |
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| Analysis of cocaine, benzoylecgonine, codeine, and morphine in hair by supercritical fluid extraction with carbon dioxide modified with methanol. | 2001 Jun 1 |
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| Effectiveness of propranolol for cocaine dependence treatment may depend on cocaine withdrawal symptom severity. | 2001 Jun 1 |
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| Urine analysis of laboratory personnel preparing cocaine training aids for a military working dog program. | 2001 Oct |
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| Rapid detection of benzoylecgonine in vitreous humor by enzyme immunoassay. | 2001 Oct |
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| Elimination of cocaine by pregnant sheep following single or multiple exposures. | 2001 Oct |
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| Effects of Stealth adulterant on immunoassay testing for drugs of abuse. | 2001 Sep |
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| Cocaine long-term administration induces myocardial depressant effects and adrenoceptors desensitization. | 2002 |
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| Endogenous gonadal hormones modulate behavioral and neurochemical responses to acute and chronic cocaine administration. | 2002 Jul 26 |
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| Simultaneous, quantitative determination of opiates, amphetamines, cocaine and benzoylecgonine in oral fluid by liquid chromatography quadrupole-time-of-flight mass spectrometry. | 2002 Nov 5 |
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| A field evaluation of five on-site drug-testing devices. | 2002 Oct |
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| A pilot trial of piracetam and ginkgo biloba for the treatment of cocaine dependence. | 2003 Apr |
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| High-performance liquid chromatographic determination of cocaine and benzoylecgonine by direct injection of human blood plasma sample into an alkyl-diol-silica (ADS) precolumn. | 2003 Feb |
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| Cyclodextrin-modified micellar electrokinetic chromatography for the analysis of Esterom, a topical product consisting of hydrolyzed benzoylecgonine in propylene glycol. | 2003 Jun |
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| Studies on metabolic pathways of cocaine and its metabolites using microsome preparations from rat organs. | 2003 Mar |
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| Measuring outcome in cocaine clinical trials: a comparison of sweat patches with urine toxicology and participant self-report. | 2003 Mar |
|
| Comparison of meconium and neonatal hair analysis for detection of gestational exposure to drugs of abuse. | 2003 Mar |
|
| Intoxication due to 1,4-butanediol. | 2003 May 5 |
Patents
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DB01515
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C005618
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DTXSID7046758
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100000085207
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BENZOYLECGONINE
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41001
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448223
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SUB21920
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208-263-5
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5353I8I6YS
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519-09-5
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m2386
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PRIMARY | Merck Index |
ACTIVE MOIETY
METABOLITE (PARENT)
